Holiday rentals in Kennebunk

An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.

4.97 out of 5 average rating, 153 reviews

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

5.0 out of 5 average rating, 325 reviews

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

A charming yellow house features white trim and black shutters, complemented by a large American flag adorning the front. Lush greenery surrounds the entry, with a neat pathway leading to the porch, where a shaded seating area is visible.

4.94 out of 5 average rating, 121 reviews

Historic Kennebunkport home .3 mile to Dock Square

Under 10 min walk to Dock Square, 2 min walk to Kennebunk River. Luxury linens, Casper pillows, SandCloud towels, Malin + Goetz toiletries, well-appointed kitchen and beach chairs included in your stay. 2 bikes & 2 kayaks available. Walk to Colony Beach, bike to Kennebunk Beach. 2 min walk to Perkins Park on the River, steps down to water for launching kayaks. Dock Square is a vacationer’s dream. Stroll along Ocean Ave on the water or grill fresh seafood on the cozy porch. 420 friendly outside

A newly renovated colonial house features a light grey exterior with black shutters and a welcoming front porch. An American flag hangs from the porch, adding a touch of character. A well-maintained garden with greenery surrounds the foundation, enhancing the quaint appearance.

5.0 out of 5 average rating, 97 reviews

Cozy updated colonial, 5 minute walk to town!

This newly renovated colonial is just a few minutes walk from Dock Square. It's lovely, airy interior is filled with antiques and modern touches. With 3 cozy bedrooms and 2 full bathrooms, it comfortably sleeps 7. The breezy open living area is the perfect spot for you, your family and guests to relax after a day at the beach, shopping or sightseeing. The private outdoor dining area is surrounded by gardens, shaded by umbrellas and has a gas fire pit for making memories after the sun goes down.

5.0 out of 5 average rating, 8 reviews

The School Street House • Dock Square Village

Featured in Decor Maine magazine, The School Street House blends historic Kennebunkport charm + modern luxury. Set on the site of the original 1820 schoolhouse and 100 steps from Dock Square, this longtime guest favorite offers 3 bedrooms, 2 baths, a chef's kitchen and inviting living spaces. Fine Italian linens, Aesop product, TOTO bidets and sun-filled interiors create a refined stay. Remarkably private for its location, the backyard opens to gardens, wildflowers and a peaceful river beyond.

5.0 out of 5 average rating, 148 reviews

A spacious studio apartment features an open layout with a fully equipped kitchen, illuminated by pendant lights above the island. A cozy living area showcases a plush couch and decorative plants, while large windows provide natural light and views of the surrounding area.

Flat in Kennebunk

Lower Village Lofts •North• Steps to Dock Square

The Lower Village Lofts *North* is a newly renovated large studio apartment located in the heart of the action - just steps from Dock Square (downtown Kennebunkport) and 1/2 mile to the beach! This unit features a brand new fully equipped kitchen, all new designer and higher end furnishings, and a custom built-in room divider complete with an electric fireplace, armoire, and 50" smart TV. The bedroom area has a new king bed with luxurious bedding, black out shades, and an additional smart TV.

4.8 out of 5 average rating, 109 reviews

The Timeless Retreat . Close Kennebunkport

Discover the newly completed 2024 full renovation of this spacious Kennebunk vacation rental, offering modern comfort and style just a 5-minute walk from downtown! With easy access to local coffee shops, restaurants, the farmers market, and the popular Garden Street Bowling Alley, this home provides the perfect base for your getaway. Perfect for a convenient escape, with a wealth of attractions just steps away to enhance your stay. Beach Parking Permit for Kennebunk Beaches included!

4.99 out of 5 average rating, 294 reviews

A charming home is surrounded by vibrant autumn foliage and a carpet of fallen leaves. The inviting exterior features a garage and large windows, while a colorful tree adds warmth to the scene. A playful atmosphere is enhanced by nearby decorations.

Guest suite in Kennebunk

The Nest! VERY CLEAN! Near downtown! Self check-in

**Please note: As of Summer 2026, Airbnb has shifted its service fee from guests to hosts. My rates & fees have been adjusted to reflect this change, not to increase my profit. The total ending cost to guests remains the same as before. :) Welcome to The Nest! We offer a beautiful private studio suite in Kennebunk, Maine! We are half a mile from downtown Kennebunk Village and less than 15 minutes to Kennebunkport and local beaches! A keyless entry makes check-in a breeze!

5.0 out of 5 average rating, 122 reviews

A cozy living area is presented with natural light filtering through large windows. A flat-screen TV is mounted on a white wall, accompanied by a wooden console. Two comfortable armchairs and a round wooden coffee table are positioned, complemented by decorative plants.

Cottage in Kennebunk

Fair Winds Cottage~1 mi to beach~

Our home, a renovated 1930’s Maine summer cottage, is located 1 mile from Kennebunk beaches and 1.5 miles from dining and shopping in Kennebunkport’s Dock Square. Close to golf, nature trails and only a 1/2 mile from the Mousam River for fishing and kayaking, it’s a great location to take in all southern coastal Maine has to offer. The cottage provides plenty of outdoor space, so come relax, dine on the back deck and take in the night sky with s'mores by the fire pit.

A two-story coastal house features a classic shingle exterior and large windows, allowing natural light to fill the interior. A wide front porch with railings offers space for seating, and a manicured lawn surrounds the property, contributing to a welcoming charm.

4.96 out of 5 average rating, 72 reviews

The Beach House - Oceanfront 5 BR

Exquisite beachfront residence on Kennebunk’s prestigious Beach Avenue, directly across from Gooch’s Beach and moments from downtown Kennebunkport. This sophisticated coastal retreat offers sweeping ocean views, gracious outdoor living, beautifully appointed interiors, and understated luxury. Ideal for memorable seaside gatherings, it blends refined comfort, timeless New England charm, and an exceptional setting for an elevated escape on the Maine coast.

A spacious living area features a large, white, slipcovered sectional sofa adorned with decorative pillows. A light wooden coffee table sits in the center, highlighted by a small potted plant. Artwork adorns the walls, and soft lighting creates a bright, inviting atmosphere.

4.97 out of 5 average rating, 375 reviews

★"Life~at~Sea"★I mi to beach★W/D★Park★2 full baths

• Open floor plan/first floor bedroom+full bath • Fully stocked kitchen with coffee & tea bar • Peaceful neighborhood close to Dock Square & less than 1 mile to KBK Beaches • Shaded back+side yard/patio/grill/outdoor shower • Netflix+Sling+Hulu+HBO+Amazon Video+4 TVs • 1 car garage parking+driveway parking for 2-3 cars • washer+dryer+towels+bed linens provided • board games, pack N plays x 2 • 2 KBK beach passes+boogie boards+beach towels+chairs

An aerial view shows a classic multi-story home positioned near the beach, surrounded by lush greenery. The coastline is visible, along with gentle waves and neighboring houses, highlighting the inviting ocean setting.

4.94 out of 5 average rating, 117 reviews

Ocean/Beach Unique Views: THE New England !

QUIET NEIGHBORHOOD, WELCOME TO FAMILIES! GAS FIREPLACE ! Classic architectural details all sited on an enviable ocean/beach location. An alluring home, lovingly maintained for 110 years, encompasses the true understated elegance of the era in which it was created. Amidst the 3,500 sq ft+, find 6 gracious bedrooms accented by 4 and a half baths, updated granite kitchen, pantry, glassed in front porch with mesmerizing views of the ever-changing sea.

Popular amenities for Kennebunk holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Kennebunk

5.0 out of 5 average rating, 66 reviews

The Cottage at Kennebunk!

Apartment in Kennebunkport

A charming two-story white house features a covered porch with railing and a central double-door entry. Lush greenery and colorful flower beds surround the property, enhancing the welcoming appearance. Large windows invite natural light, and the roof is adorned with shingles.

Luxury Coastal Retreat | Mins from Dock Square

4.99 out of 5 average rating, 70 reviews

A sunlit corner features a light-colored armchair alongside a small, round side table. Large glass doors open to a natural setting, while a stylish floor lamp adds warmth to the contemporary space. Wooden bar stools are arranged at the kitchen counter.

4.96 out of 5 average rating, 80 reviews

New home, amazing location

A charming coastal house is surrounded by a white picket fence and lush green grass. The exterior features wooden shingles and a gray roof, complemented by several windows that reflect the clear blue sky. Mature trees can be seen in the background.

5.0 out of 5 average rating, 14 reviews

New dates. Renovated! Steps away from Gooch Beach!

An inviting garden patio is showcased, featuring a mix of stone and grass pathways. Two seating areas are visible, including a wicker chair with cushions and a white metal chair. Colorful flowers and greenery adorn the space, offering a serene outdoor atmosphere.

4.88 out of 5 average rating, 65 reviews

Kozy Kottage - Parsons Beach 2 miles

5.0 out of 5 average rating, 36 reviews

Cozy Dock Square Kennebunkport Cottage

4.96 out of 5 average rating, 56 reviews

A two-story cottage features a light grey exterior with navy shutters. The front porch includes seating and a gas grill. Lush green grass and trees surround the cottage, providing a pleasant outdoor atmosphere.

Cottage in Kennebunk

Ocean view cottage, walk to Kennebunk Beach

Superhost